Bear Happy Hour

Chicago's kinkiest karaoke night lands every Wednesday at Jackhammer—a midweek release where bold performances and uninhibited energy take over. Whether you're stepping up to the mic or watching the chaos unfold, this is the kind of unpretentious, no-judgment space where self-expression is the whole point. Free to attend, first-come, first-served; sign-ups happen in person.

The monthly invitation to suit up and step into the leather and gear scene. Dedicated to showcasing leather, rubber, harnesses, hoods, and everything in between, this night brings together a packed room of people who understand the assignment. Whether you're building a collection or trying your first piece, expect bold looks, confident energy, and a community that celebrates self-expression. Free before 10pm.

Twenty years of Chicago Rubber Club history comes alive at Jackhammer — a night celebrating the leather and rubber community that's defined the scene. Expect the crowd that's been there from the start, the energy that keeps it going, and a room full of people who know exactly what this milestone means.

Team Vespertine takes over The Hole for a summer birthday celebration of their dear Ammunition — four hours of interactive fetish play, education, and community in Jackhammer's legendary subterranean space. Open to queer women, trans folks, and non-binary folks 21+. Whether you're here to play, learn, or just connect with like-minded people, there's room for you. Fetish dress code strictly enforced; complimentary bag check, safer sex kits, and snacks provided. $30 tickets in advance only.

Summer camp for grown-ups hits the dance floor at Jackhammer. Pack your gear, embrace the playful energy, and dance until sunrise with DJ Baby Davee spinning classic hits all night long. Whether you're rocking scout-inspired fits or keeping it cozy, this is your chance to tap into the fun and mischief that make summer unforgettable. Free changing supplies provided.

Sunday afternoon gathering at Jackhammer for the leather and alternative community. Pool, darts, drinks, and good company — the kind of low-key social that's become a neighborhood staple.